He has a rather disjointed/disconnected chart.
Hi Katy, thanks for your reply!! You know, the whole acting cool and rebellious does sound a lot like him! It's true! He definitely projects that image to the world. He also acts very sarcastic and cynical but like I said, he truly is sensitive and loving under the surface.
And I'm sure he does love her, after all they've known each other for many years, but the thing I'm mostly worried about is that he has been very specific about not being IN love with her, and he even confessed to wanting to fall in love... I certainly think there's lots of denial involved and as years passed, he couldn't really accept the relationship kind of "failed"...
What I mean by this is he always referred to her as just a friend, and according to what he told me, she pretty much "pressured" him into a more committed relationship... And of course, this could also be a distortion, or him acting cool and detached but truth is: I haven't seen him truly happy throughout these years, he's actually been really unstable, frustrated, even depressive sometimes.
I also always thought he was using the infidelities and "double life" as a "single" person as an escape and indication that he desires to meet new people and even find true love... It's not like he went around having one night stands, it was like a full "parallel" relationship. Which is pretty in tune with his deep emotional needs and attachment that you mentioned.
That's why I think he's making a mistake but I can't really help him because he's too stubborn... I told him to at least go see a therapist but he doesn't even want to do that.
Like you said, I guess Venus in cancer in the 7th makes him "need" the committed relationship, though.
Also, the bit about "loving in the way he knows to love" might be why my friend who looked at his chart said he "can't" fall in love... Maybe they meant he loves differently than most people. He's very aware that the way he acted was wrong, though (he even hates cheating ironically, 'cause he's been cheated on a previous relationship and was really hurt)